Wordy. Dirty. QWERTY.

As a freelance writer, you’re often required to write an inquiry letter, or cover letter, that you submit with your samples and resume. This letter is to be classy and original, witty without being glib, a brief showcase of all your good traits, with a come hither final line that seals the proverbial deal. In short, it’s, like, the most difficult thing to write, like, ever.

In my professional experience I’ve had to pen my fair share of cover letters, usually for administrative assistant positions. I’ve followed a formula that I was taught early on, and I’ve always relied on my ability to isolate details, about myself and the desired position, that play well together. Often this is reflexively helpful, if I find myself stumped for a reason as to why or how I’d be good for the position it’s often a sign that I shouldn’t bother to apply.

Being raised by a woman who, for whatever unknown reason, wanted to install in her only child a set of rigid and dated manners along with a fear of authority reminiscent of the musical Les Mis, I have weird and extreme etiquette. I basically assume I am everybody’s humble servant and, just short of curtsying, I will treat you like you own me…for the first five minutes I meet you. After that, unless it’s an actual job interview, the “fucks,” “cunts,” and garden-variety vagina jokes come out.

After an ex-girlfriend’s mother berated me, violently, for calling her Mrs. Ex-Girlfriend’s Last Name, I’ve become a bit more world weary and less inclined to manner my way to the throne.

What does this have to do with cover letters? Everything. The usual rigmarole, for me at least, is a semi-formal affair. While it’s no black tie ball — I don’t use conventional business letter formatting or, yikes, snail mail — I do speak to the recipient as though they are, say, Tony Blair. Or God. It’s nothing, if not professional.

But what about the boutique company, the small seven-person firm looking for a writer, the quirky and down-to-earth client who will hire you more for your personality than for your ability to wear a skirt suit and heels? Those jobs require an important and incredibly difficult part of the freelance repertoire: the colloquial cover letter.

I imagine this sort of tonal dissonance is encountered by adults writing PSAs for teens, or writers for Spin magazine when they interview a semi-famous band. (“Bro, do you think open source media is lame or rad?”) It’s a strange note to try to hit, the one between reverent and, well, irreverent. Here are the three key points that I have discovered that I can share with those of you looking to kick back, relax, and cobble together the informal letter that gets you hired. Just remember to send me a cut of your first paycheck.

One: It Is Still Like Football

That is to say, you should outline your course of action before writing the thing. As most high-school graduates have learned when they were taught how to construct a solid five paragraph essay, building the skeleton of key points prior to fleshing out the text is the best way to keep any sort of text concise, hard-hitting, and wholly on track. Otherwise you wind up being long winded, and the only job that being too talky guarantees you is to go and pick up somebody’s dry cleaning. Or maybe that’s just me.

Two: This Is Not Facebook

It is tempting to use the informal inquiry to showcase how spectacularly funny and hip you are. After all, you can write on the cutting edge, why not prove it? The answer is because this is a job, not a popularity contest.

Often as I was starting out freelancing I tried to prove my unequivocal greatness by submitting too much, an onslaught of samples coupled with letters that, in hindsight, came across as pompous and condescending. Of course that hadn’t been my intent, it’s just that, naturally, I felt insecure about the hiring process, so I tried to overcompensate. What I thought came across as phenomenally cool and revealing actually was overbearing and masturbatory. You wouldn’t masturbate in a job interview, would you? (If you answered yes I am hiring.)

The cover letter is a lot like a first date. You want to tell them a little bit about how great you are, but no need to harp on your ex-girlfriend, or what kinky bedroom games you’re interested in playing. Less is more, especially if that less is awesome.

Three: Profread.

Ha. Get it?

My fatal flaw (other than my insatiable sex drive and the fact that I’m a sushi-loving vegan) is editing my own work. I’ve gotten better at it, thanks mainly to Simon, who has the opposite problem of never feeling fully finished with a piece of work due to an addiction to scrutiny. I cannot stress enough how, in an informal letter especially, it is vital to make sure you’ve used proper grammar, perfect spelling, and on-point punctuation. When you’re employing a less fancy method of conveying how talented and capable you are, the last thing you want it to sound like is a fifteen year old girl’s text message from the mall. U r g8, yes, but make sure your future employer knows that you understand business syntax, too.

There are other tiny nuggets of wisdom: use a comma, not a colon after your introduction, use contractions to make the tone more easygoing, feel free to write “Dear” in place of “To Whom It May Concern,” and don’t shy away from brief personal statements. Basic stuff that seems like common sense.

Of course, you can write all of this advice off because I’m barely able to pay my rent this month, and I’m hoping that this guidance translates to my own professional success in the coming weeks.

If I don’t hear back I’ll let you know it’s bunk, and write a post on how to write the perfect desperate one-sentence plea that can be scribed in Sharpie on a piece of cardboard.

I’m grateful to everyone who reads this, but especially to you crazy kids who donate. It means a lot and it keeps me fed. (And sheltered, this month.) AinsleyDrew at gmail, because I have no hobbies other than this blog I will most certainly write you back.

[Note: If you, or someone you know, is looking for one or two freelance writers, for everything from cover letters to wedding vows, site copy or eulogies, editorial articles or whitepapers, letters of resignation from your crappy job or love letters to that girl across the hall, let me know. AinsleyDrew at gmail. Our rates are reasonable, unlike drunk ex-girlfriends.]
Seemingly Awesome Jobs That I Do Not Want

Comic book writer

Vasquez. Dirge. Valentino. Sfar. Ohba. Rugg and Maruca. Mizuno. I love graphic novels and comics of all varieties, but especially the ones for pouty teenagers who wear all black and spend their allowances at Hot Topic. (My inner child writes angry poetry, carries a metal lunchbox, and wears her Tool tee-shirt every day.) Why not apply my interest to my career? After all, I do have a degree in dramatic writing.

Because I am already broke, that‘s why. Most comic book writers get paid $500 for a script by small companies. $500 for a twenty-two page script would mean that a) I’d need to have two guaranteed deals a month in order to simply pay my bills and break even and b) I would basically be in the same position that I’m in now, only I likely wouldn’t have the freedom to consistently write in my own voice, with vagina jokes galore.

But in case you’re interested in panel-by-panel panhandling, check out the Comic Book Resources page.

Stripper

Where I grew up on Long Island, being a stripper was easy money. A few of my friends made a decent living at it, and actually seemed to enjoy what they did. They were able to afford regular manicures, they had funny stories to tell when out to lunch, and they looked forward to going to work, which, to me, is the most important part of any career. I figure that I like music, and I like dancing, and I like being naked. Getting a job as a stripper seems like a no-brainer.

Except most exotic dancers retire at 28 (that’s eleven months away for yours truly) and I get sleepy after midnight. When I’m sleepy I’m also cranky, and often say things like, “I‘m gonna eat your dick.” Dancing two or three three-hour long shifts, coupled with having to act as though I like strangers when I’m a natural misanthrope, topped off by the fact that ever since I started dating Simon I’ve had some severe difficulty when it comes to acting interested in anyone but him…well, I probably wouldn’t make it past the audition stage anyway. For one thing, I have the rhythm of a half-Jewish white girl who likes synthpop. Also, I have no bilateral symmetry. Unless you are looking at me as though I am a boy.

I must warn you, even if you don’t want to be an exotic dancer, if you check out Stripper FAQ you will lose half of your day to reading. Yes, reading the articles. Swear. The author, Kiko Wu, is a decent writer with a lot to share. Um. Yeah, that’s pretty much as expertly as I can put that.

Stripper Resource is great, too, but NSFW. Unless you work out of your home like I do. Then it’s just not safe for productivity.
Rock star

I’m sober and a homebody. Even if I enjoy wearing my lingerie outside of my clothes, giving strangers the finger, and “expressing myself,” my lack of musical skills and enjoyment of things like cooking paella and reading Martha Stewart Living render this career option null and void.

I would gladly be Maynard James Keenan’s assistant, though. It’s close enough, I have the credentials, and he’d probably laugh at my vag jokes. Everybody wins.

Maynard James Keenan resources, ’cause “rock star resources” only exist in an open bar or concert venue.

On my last day in New York I was driving down Main Street in Port Washington and got stopped behind a Lexus. Affixed to the bumper of said automobile was the bumper sticker reading

HYPNOTISTS ARE ENTRANCING

There was a tiny spiral that resembled a thumbprint on the left side of this statement.

Simon joked that I should rear-end the car and then say, “Sorry, I was distracted by your bumper sticker.”

When I pointed out, with bitter envy, that the sticker should read LEXUS OWNERS ARE GULLIBLE, I was informed by my counterpart that professional hypnotists make loads of money.

Really.

"No, my mustache is better!"

People stare at me a lot. I have a rhythmic, if somewhat grating, giggle. I’m not afraid to watch people sleep. I really, really need some cash.

Maybe I should be a professional hypnotist.

For those of you who are of generation MySpace, allow me to explain. Hypnosis, or hypnotherapy, is a method of harnessing the subconscious by inducing a trance-like state. It’s often associated with the New Age movement, natural healers, holistic health, Ouija Boards, and goths. It can be used to help cure anything from kicking cancer sticks to social anxiety to binge eating to having too much money. I’m skeptical, but then again, I hate everything. Maybe a hypnotist can help.

The American Psychological Association is quoted as saying that hypnosis itself can cause “…changes in subjective experience, alterations in perception, sensation, emotion, thought or behavior.” Proponents believe it can help decrease cravings, enhance physical performance, and even act as a painkiller for things as intense as childbirth. To which I say, yeah, okay. You try deep breathing as your method of coping with your cervix dilating to the point of passing a honeydew melon through your vagina, I’ll tell you that you’re cuckoo for Cocoa-Puffs. But the application of hypnosis for medicinal purposes has been around since the late 1800s, and very few phony fads have that kind of staying power. In 1958 the American Medical Association published a report that can be summed up with the line “…the use of hypnosis has a recognized place in the medical armamentarium and is a useful technique in the treatment of certain illnesses when employed by qualified medical and dental personnel.” (“Medical use of hypnosis”, JAMA, 1958)

So even if I personally have my doubts, hypnosis is not a slap bracelet.

Also, don’t get hypnosists confused with those who practice mesmerizing. I get the impression that they’re offended by that. Kind of like an Irish versus Scottish thing.

In order to become a hypnotist you have to go to school, and get certification by one of the very few accredited hypnosis organizations, such as the American Council of Hypnotist Examiners. The group was founded in 1973 to self-regulate the practitioners of hypnosis and make sure that they didn’t all bond together to create some malevolent plan to make the human race their army of flesh-eating cannibal zombies that would eventually require Batman to come and destroy them and save Gotham. The ACHE explains the guidelines that you’re required to follow in order to become a certified hypnotist. They basically include between 200 and 300 hours of instruction and testing. I assume you have to also pledge to fight the forces of Grayskull or something, but I will never know, for it also requires $175 in order to receive registration and two years of certification. I do not have $175 to my name at this point. But, hey, thanks for playing.

Moreover, hypnosis itself is pretty thoroughly routed in a subject’s ability to succumb to the power of suggestion and, oh yeah, relax. It would be very similar to me attempting to perform an exam for Ipsilateral Testicular Hypotrophy. Google it.

Basically, in brief, I don’t have the money to become a hypnotist, which is good, ‘cause it’s probably something that I wouldn’t have a natural knack for. It’s likely that I’ll become a Lexus owner before I become a relaxation guru.